Flight Deals from San Francisco to Chicago from $98
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Price Drop Deals Near You
Chicago
53% Price Drop
Aug 30
SFO
4 days
Sep 3
ORD
$416
now only
$197
Rond Trip
Chicago
31% Price Drop
Jun 30
SFO
4 days
Jul 4
MDW
$360
now only
$248
Rond Trip
Chicago
51% Price Drop
Jul 17
SFO
5 days
Jul 22
ORD
$416
now only
$206
Rond Trip
Chicago
51% Price Drop
Jul 24
SFO
5 days
Jul 29
ORD
$417
now only
$206
Rond Trip
Chicago
48% Price Drop
Aug 15
SFO
3 days
Aug 18
ORD
$416
now only
$216
Rond Trip
Chicago
44% Price Drop
Jun 30
SFO
4 days
Jul 4
ORD
$416
now only
$232
Rond Trip
Chicago
41% Price Drop
Jul 1
SFO
3 days
Jul 4
ORD
$417
now only
$248
Rond Trip
Chicago
39% Price Drop
Jul 12
SFO
4 days
Jul 16
ORD
$417
now only
$255
Rond Trip
Chicago
27% Price Drop
Jul 23
SFO
5 days
Jul 28
MDW
$360
now only
$264
Rond Trip
Chicago
20% Price Drop
Jul 23
SFO
4 days
Jul 27
MDW
$360
now only
$290
Rond Trip
Stops
Nonstop
from $196
Up to 1 stop
$216
Up to 2 stops
$261
Airlines
Alaska Airlines
$196
American Airlines
$216
Delta Air Lines
$256
Frontier Airlines
$305
Hahn Air
$339
Hawaiian Airlines
$196
Southwest Airlines
$236
United Airlines
$273
Cabin Class
Economy
$196
Departure Airports
San Francisco International Airport
$196
Arrival Airports
Chicago Midway Airport
$256
Chicago O Hare Airport
$196
Layover Airports
Dallas Fort Worth International Airport
$315
Denver International Airport
$236
Detroit Metropolitan Airport
$256
Hartsfield Jackson Atlanta International Airport
$256
Los Angeles International Airport
$286
Minneapolis-St Paul International/Wold-Chamberlain Airport
$256
Orlando International Airport
$310
Phoenix Sky Harbor International Airport
$363
Portland International Airport
$216
Salt Lake City International Airport
$256
Seattle Tacoma International Airport
$216
Best Price. GUARANTEED.
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BUNDLE & SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Hawaiian Airlines
08/12/25
SFO
6h 23m
Direct
08/12/25
ORD
Hawaiian Airlines
08/19/25
ORD
2h 48m
Direct
08/19/25
SFO
$196
Alaska Airlines
08/12/25
SFO
6h 23m
Direct
08/12/25
ORD
Alaska Airlines
08/19/25
ORD
2h 48m
Direct
08/19/25
SFO
$196
Alaska Airlines
08/06/25
SFO
6h 23m
Direct
08/06/25
ORD
Alaska Airlines
08/12/25
ORD
2h 48m
Direct
08/12/25
SFO
$196
Hawaiian Airlines
08/05/25
SFO
6h 23m
Direct
08/05/25
ORD
Hawaiian Airlines
08/07/25
ORD
2h 48m
Direct
08/07/25
SFO
$206
Hawaiian Airlines
08/06/25
SFO
10h 47m
SEA
08/07/25
ORD
Hawaiian Airlines
08/13/25
ORD
2h 48m
Direct
08/13/25
SFO
$216
Hawaiian Airlines
08/13/25
SFO
8h 34m
PDX
08/13/25
ORD
Hawaiian Airlines
08/16/25
ORD
2h 48m
Direct
08/16/25
SFO
$216
American Airlines
08/08/25
SFO
6h 16m
Direct
08/09/25
ORD
American Airlines
08/11/25
ORD
2h 30m
Direct
08/11/25
SFO
$216
Hawaiian Airlines
08/12/25
SFO
9h 14m
SEA
08/12/25
ORD
Hawaiian Airlines
08/16/25
ORD
2h 48m
Direct
08/16/25
SFO
$216
Alaska Airlines
08/06/25
SFO
6h 23m
Direct
08/06/25
ORD
Alaska Airlines
08/12/25
ORD
5h 24m
PDX
08/12/25
SFO
$216
Southwest Airlines
08/08/25
SFO
10h 15m
DEN
08/08/25
ORD
Southwest Airlines
08/11/25
ORD
9h 25m
DEN
08/11/25
SFO
$236
Delta Air Lines
08/10/25
SFO
7h 35m
MSP
08/10/25
ORD
Delta Air Lines
08/15/25
ORD
7h 33m
SLC
08/15/25
SFO
$256
Delta Air Lines
08/06/25
SFO
9h 4m
DTW
08/07/25
MDW
Delta Air Lines
08/19/25
MDW
4h 28m
SLC
08/19/25
SFO
$256
Delta Air Lines
08/26/25
SFO
11h 37m
DTW
08/26/25
MDW
Delta Air Lines
08/29/25
MDW
4h 21m
SLC
08/29/25
SFO
$256
Delta Air Lines
08/20/25
SFO
10h 18m
ATL
08/20/25
MDW
Delta Air Lines
08/27/25
MDW
8h 24m
ATL
08/27/25
SFO
$256
Delta Air Lines
08/05/25
SFO
7h 55m
MSP
08/05/25
MDW
Delta Air Lines
08/27/25
MDW
5h 36m
SEA
08/27/25
SFO
$256
Delta Air Lines
08/26/25
SFO
9h 13m
DTW
08/26/25
ORD
Delta Air Lines
08/30/25
ORD
6h 45m
DTW
SLC
08/30/25
SFO
$261
Delta Air Lines
08/25/25
SFO
8h 10m
MSP
08/25/25
MDW
Delta Air Lines
09/03/25
MDW
6h 46m
DTW
SLC
09/03/25
SFO
$261
United Airlines
08/16/25
SFO
6h 14m
Direct
08/17/25
ORD
United Airlines
08/31/25
ORD
2h 46m
Direct
08/31/25
SFO
$273
United Airlines
08/26/25
SFO
6h 17m
Direct
08/26/25
ORD
United Airlines
08/31/25
ORD
2h 42m
Direct
08/31/25
SFO
$273
American Airlines
08/26/25
SFO
6h 21m
Direct
08/26/25
ORD
American Airlines
09/02/25
ORD
2h 33m
Direct
09/02/25
SFO
$286
American Airlines
08/08/25
SFO
6h 16m
Direct
08/09/25
ORD
American Airlines
08/11/25
ORD
4h 34m
LAX
08/11/25
SFO
$286
Frontier Airlines
08/05/25
SFO
12h 37m
ATL
08/06/25
MDW
Frontier Airlines
08/12/25
MDW
9h 8m
ATL
08/12/25
SFO
$305
Frontier Airlines
07/29/25
SFO
12h 37m
ATL
07/30/25
MDW
Frontier Airlines
08/05/25
MDW
9h 8m
ATL
08/05/25
SFO
$305
Delta Air Lines
08/18/25
SFO
12h 29m
ATL
08/19/25
ORD
Delta Air Lines
09/02/25
ORD
8h 39m
MSP
LAX
09/02/25
SFO
$309
Frontier Airlines
08/08/25
SFO
11h 14m
MCO
08/09/25
ORD
Frontier Airlines
08/11/25
ORD
17h 25m
MCO
08/12/25
SFO
$310
Frontier Airlines
07/31/25
SFO
12h 19m
DFW
08/01/25
MDW
Frontier Airlines
08/07/25
MDW
6h 28m
ATL
08/07/25
SFO
$315
Frontier Airlines
08/14/25
SFO
12h 7m
DFW
08/15/25
ORD
Frontier Airlines
08/21/25
ORD
5h 29m
DEN
08/21/25
SFO
$315
Hahn Air
08/18/25
SFO
6h 23m
Direct
08/18/25
ORD
Hahn Air
08/19/25
ORD
2h 48m
Direct
08/19/25
SFO
$339
Hahn Air
08/05/25
SFO
6h 23m
Direct
08/05/25
ORD
Hahn Air
08/07/25
ORD
2h 48m
Direct
08/07/25
SFO
$339
American Airlines
08/07/25
SFO
9h 14m
PHX
08/08/25
ORD
American Airlines
08/12/25
ORD
2h 33m
Direct
08/12/25
SFO
$363
Top Deals on flights from San Francisco to Chicago
San Francisco, US (SFO) - Chicago, US (CHI)
Hawaiian Airlines
Aug 2
SFO
6h 23m
Direct
Aug 2
ORD
as low as
$98
San Francisco, US (SFO) - Chicago, US (CHI)
Alaska Airlines
Aug 5
SFO
6h 23m
Direct
Aug 5
ORD
as low as
$98
San Francisco, US (SFO) - Chicago, US (CHI)
Hawaiian Airlines
Aug 5
SFO
9h 14m
SEA
Aug 5
ORD
as low as
$118
San Francisco, US (SFO) - Chicago, US (CHI)
Alaska Airlines
Aug 5
SFO
8h 34m
PDX
Aug 5
ORD
as low as
$118
San Francisco, US (SFO) - Chicago, US (CHI)
Delta Air Lines
Jul 15
SFO
8h 51m
SLC
Jul 15
ORD
as low as
$128
San Francisco, US (SFO) - Chicago, US (CHI)
Delta Air Lines
Jul 12
SFO
10h 28m
ATL
Jul 13
ORD
as low as
$128
San Francisco, US (SFO) - Chicago, US (CHI)
Delta Air Lines
Jul 24
SFO
9h 9m
DTW
Jul 25
ORD
as low as
$128
San Francisco, US (SFO) - Chicago, US (CHI)
Delta Air Lines
Aug 2
SFO
7h 35m
MSP
Aug 2
ORD
as low as
$128
San Francisco, US (SFO) - Chicago, US (CHI)
Delta Air Lines
Aug 5
SFO
9h 4m
DTW
Aug 6
MDW
as low as
$128
San Francisco, US (SFO) - Chicago, US (CHI)
Southwest Airlines
Jul 16
SFO
18h 15m
LAS
Jul 16
ORD
as low as
$137
San Francisco, US (SFO) - Chicago, US (CHI)
Frontier Airlines
Jul 18
SFO
11h 14m
MCO
Jul 19
ORD
as low as
$137
San Francisco, US (SFO) - Chicago, US (CHI)
American Airlines
Jul 22
SFO
6h 18m
Direct
Jul 23
ORD
as low as
$143
Frequently Asked Questions
What is the typical flight duration from San Francisco to Chicago?
The typical direct flight from San Francisco to Chicago takes between 4 to 5 hours, depending on weather conditions and the specific flight path chosen. While your journey is generally consistent, variations might occur due to air traffic or runway usage. It is advisable to check your flight status closer to departure, as even minor delays can extend your travel time. Planning extra time for boarding and possible layovers ensures a smoother overall travel experience between these two major cities.
Are there any direct flights from San Francisco to Chicago?
Yes, there are direct flights available from San Francisco to Chicago. Major carriers like United Airlines and American Airlines frequently operate non-stop services, which typically range in frequency throughout the week. Direct flights are a faster option compared to itineraries with layovers, helping you reach your destination more efficiently. However, schedules can change seasonally and based on travel demand, so reviewing current flight availability and booking early can secure better fares and preferred flight times for your trip.
What are the best transportation options from Chicago airport to downtown?
Travelers arriving at Chicago’s airports have several efficient transportation options to reach downtown. One practical choice is the Blue Line train, which typically takes between 35 to 50 minutes with fares ranging from $5 to $10. Additionally, rideshare services and taxis offer door-to-door convenience with costs around $30 to $70, depending on traffic. Some hotels also provide shuttle services. Checking current fare estimates and schedules ahead of time will help you make an informed decision based on your travel itinerary and budget needs.
What are the must-see attractions in Chicago for travelers arriving from San Francisco?
Travelers should explore several key attractions during their visit. Highlights include Millennium Park, known for its iconic Cloud Gate sculpture, and the Art Institute of Chicago, which offers a rich collection of artworks. Navy Pier provides diverse dining and entertainment options, while a visit to Willis Tower Skydeck promises breathtaking city views. These sites provide a vibrant mix of culture, art, and urban exploration that differentiates this destination from San Francisco's landmarks.
Which local dishes should travelers from San Francisco try when visiting Chicago?
When exploring the local cuisine, visitors should sample Chicago-style deep-dish pizza and the renowned Chicago-style hot dogs, which are prepared with unique toppings and a distinctive style. Additionally, Italian beef sandwiches and Chicago’s diverse ethnic fare are must-tries. Restaurant prices typically range from $15 to $30 per meal, allowing you to explore both upscale dining and casual eateries with authentic flavors. Each dish offers a unique taste of the local culinary scene, providing a delicious contrast to the fare found in San Francisco.
Are there any family-friendly activities in Chicago for visitors from San Francisco?
Yes, there are numerous family-friendly activities available. Highlights include the interactive exhibits at the Museum of Science and Industry and the fascinating displays at the Shedd Aquarium. The Lincoln Park Zoo offers free admission and engaging outdoor activities. These options provide educational and entertaining experiences for all ages. Additionally, there are several parks and community events that cater to families, ensuring a fun and well-rounded visit that can appeal to the playful interests of visitors accustomed to the dynamic offerings in San Francisco.
What are the best budget-friendly hotels in Chicago for travelers from San Francisco?
Budget-conscious travelers can find several options in Chicago without compromising comfort. Many budget-friendly hotels and hostels in central locations offer rates between $100 to $200 per night. Establishments near public transit hubs like the Loop provide easy access to attractions. Options such as boutique inns and well-rated chain hotels often feature essential amenities, making them great bases for exploring culture and dining. It is wise to book in advance and check recent reviews to ensure that the chosen option aligns with your budget and travel expectations.
What are the top cultural experiences in Chicago that travelers from San Francisco should not miss?
Chicago offers an array of cultural experiences that stand out. Consider taking an architecture river cruise to appreciate the city’s famous skyline and historic structures, followed by a visit to the Art Institute of Chicago for its impressive art collections. The Theater District and live music venues provide additional cultural immersion. Exploring neighborhoods like Pilsen or Bronzeville can also reveal vibrant local arts and community stories. Each experience enriches your visit with a blend of history and modern creativity, offering a unique atmosphere distinct from San Francisco.
What are the safety tips for travelers from San Francisco visiting Chicago?
Safety remains a priority for visitors, so it’s recommended to stay aware of your surroundings, especially in crowded areas or when using public transit. Keep personal belongings secure and avoid isolated areas late at night. Use well-reviewed transportation services and follow local guidance. It also helps to have a working mobile phone and emergency contact details for local authorities. In case of unexpected situations, knowing the location of nearby police stations or tourist help centers can provide additional reassurance, ensuring your visit is as comfortable and safe as possible.
Is there a specific time of year when Chicago is best visited by travelers from San Francisco?
The optimal time to visit Chicago is generally during late spring to early fall. These months offer mild weather conditions, with temperatures typically ranging from 60°F to 80°F, making outdoor attractions and festivals very enjoyable. While summers can be lively with various events, spring and fall provide a balance between fewer crowds and pleasant temperatures. Winter visits might appeal to those who enjoy snowy cityscapes, though temperatures can drop significantly. Planning your trip during the shoulder seasons generally offers more comfortable sightseeing conditions.
What are the best places to shop for souvenirs in Chicago for travelers from San Francisco?
For a memorable shopping experience, consider visiting the Magnificent Mile, which hosts an array of specialty stores offering distinctive souvenirs. Navy Pier also has several boutiques featuring locally crafted items. Additionally, neighborhoods known for their art and vintage shops provide unique pieces that capture the essence of the city. Prices typically range from $10 to $100, giving you flexibility depending on your budget. Each venue offers a curated selection of items, ensuring a meaningful and self-expressive gift or memento from your trip.
What are the unique airport amenities in Chicago for travelers arriving from San Francisco?
Chicago airports offer a range of unique amenities aimed at enhancing your travel experience. At terminals like O’Hare and Midway, you can enjoy locally inspired dining options, art installations, and retail spaces that showcase regional products. Free Wi-Fi, comfortable lounges, and in some cases spa services provide added convenience. Some terminals even feature play areas for children and quiet zones for business travelers. These thoughtfully curated spaces help make the waiting time more productive and enjoyable, giving you a preview of the city’s vibrant culture before you venture into downtown.
Are there any seasonal events in Chicago that travelers from San Francisco should not miss?
Yes, Chicago hosts several seasonal events that are worth planning around. Summer brings the Chicago Air and Water Show and Taste of Chicago, offering dynamic cultural and culinary experiences. In the fall, festivals celebrating art, music, and local heritage add vibrancy to the cityscape. Winter features festive markets like the Christkindlmarket, creating a cozy atmosphere despite the cold. Each event provides an opportunity to immerse yourself in the city’s local traditions and vibrant community life, ensuring that your visit is enriched by unique seasonal celebrations.
What are the customs requirements for travelers flying from San Francisco to Chicago?
For domestic travel between San Francisco and Chicago, there are no customs requirements, as both cities are within the United States. However, all travelers must present a valid government-issued photo identification in accordance with TSA regulations. It’s also important to be aware of security screening procedures, carry-on restrictions, and any recent updates regarding travel guidelines. Preparing these documents and reviewing the Transportation Security Administration’s website ahead of your trip can help ensure a smooth and compliant experience at the airport.
What are the best solo travel activities in Chicago for travelers arriving from San Francisco?
Solo travelers in Chicago have a wide range of activities to enjoy. Consider exploring independent walking tours of the city’s architectural marvels, which typically run for 1 to 2 hours and provide in-depth historical insights. Visits to museums like the Art Institute or local galleries offer enriching experiences, often at reasonable admission prices ranging from $15 to $30. Additionally, participating in food tours or attending cultural events can facilitate meeting others while enjoying the city’s vibrant atmosphere. Such activities provide both personal enrichment and safe opportunities to immerse yourself in urban life.